- Aminophylline
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Aminophylline 
Systematic (IUPAC) name 1,3-dimethyl-7H-purine-2,6-dione; ethane-1,2-diamine Clinical data AHFS/Drugs.com Consumer Drug Information MedlinePlus a601015 Pregnancy cat. ? Legal status P (UK) Routes oral, i.v. Pharmacokinetic data Protein binding 60% Half-life 7-9 hours Identifiers CAS number 317-34-0 
ATC code R03DA05 PubChem CID 9433 DrugBank APRD00329 ChemSpider 9062 UNII 27Y3KJK423 KEGG D00227 ChEMBL CHEMBL1210 
Chemical data Formula C16H24N10O4 Mol. mass 420.427 g/mol SMILES eMolecules & PubChem - InChI=1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2
Key:FQPFAHBPWDRTLU-UHFFFAOYSA-N
(what is this?) (verify)Aminophylline is a bronchodilator. It is a compound of the bronchodilator theophylline with ethylenediamine in 2:1 ratio. The ethylenediamine improves solubility, and the aminophylline is usually found as a dihydrate[1]
Contents
Properties
It is more soluble in water than theophylline. White or slightly yellowish granules or powder, having a slight ammoniacal odor and a bitter taste. Upon exposure to air, it gradually loses ethylenediamine and absorbs carbon dioxide with the liberation of free theophylline. Its solutions are alkaline. One g dissolves in 25 mL of water to give a clear solution; 1 g dissolved in 5 mL of water crystallizes upon standing, but redissolves when a small amount of ethylenediamine is added. Insoluble in alcohol and in ether.
Mechanism of action
Like other methylated xanthine derivatives, aminophylline is both a
- competitive nonselective phosphodiesterase inhibitor [2] which raises intracellular cAMP, activates PKA, inhibits TNF-alpha [3][4] and leukotriene [5] synthesis, and reduces inflammation and innate immunity [5] and
- nonselective adenosine receptor antagonist.[6]
Aminophylline is less potent and shorter-acting than theophylline. Its most common use is in the treatment of bronchial asthma.
Causes bronchodilatation, diuresis, CNS and cardiac stimulation, and gastric acid secretion by blocking phosphodiesterase which increases tissue concentrations of cyclic adenine monophosphate (cAMP) which in turn promotes catecholamine stimulation of lipolysis, glycogenolysis, and gluconeogenesis and induces release of epinephrine from adrenal medulla cells
Other uses
Aminophylline is used to reverse dypridamole or adenosine based infusions during nuclear cardiology stress testing.
Aminophylline has shown some promise as a bodyfat reducer when used as a topical cream (sometimes referred to as "cutting gel").[7] Aminophylline is also a treatment option for anaphylactic shock.[8]
Brand names
- Phyllocontin
- Truphylline
- Minomal R 175 mg tab
- Minomal R 350 mg tab
- Minomal SR 600 mg tab
References
- ^ "Aminophylline Professional Monograph". http://www.drugs.com/pro/aminophylline-injection.html.
- ^ Essayan DM. (2001). "Cyclic nucleotide phosphodiesterases.". J Allergy Clin Immunol. 108 (5): 671–80. doi:10.1067/mai.2001.119555. PMID 11692087.
- ^ Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R. (2008). "Insights into the regulation of TNF-alpha production in human mononuclear cells: the effects of non-specific phosphodiesterase inhibition.". Clinics (Sao Paulo). 63 (3): 321–8. doi:10.1590/S1807-59322008000300006. PMC 2664230. PMID 18568240. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2664230.
- ^ Marques LJ, Zheng L, Poulakis N, Guzman J, Costabel U (February 1999). "Pentoxifylline inhibits TNF-alpha production from human alveolar macrophages". Am. J. Respir. Crit. Care Med. 159 (2): 508–11. PMID 9927365. http://ajrccm.atsjournals.org/cgi/pmidlookup?view=long&pmid=9927365.
- ^ a b Peters-Golden M, Canetti C, Mancuso P, Coffey MJ. (2005). "Leukotrienes: underappreciated mediators of innate immune responses.". J Immunol. 174 (2): 589–94. PMID 15634873. http://www.jimmunol.org/cgi/content/full/174/2/589.
- ^ Daly JW, Jacobson KA, Ukena D. (1987). "Adenosine receptors: development of selective agonists and antagonists.". Prog Clin Biol Res. 230 (1): 41–632. PMID 3588607.
- ^ Caruso MK, Pekarovic S, Raum WJ, Greenway F (May 2007). "Topical fat reduction from the waist". Diabetes, obesity & metabolism 9 (3): 300–3. doi:10.1111/j.1463-1326.2006.00600.x. PMID 17391155. http://www.blackwell-synergy.com/openurl?genre=article&sid=nlm:pubmed&issn=1462-8902&date=2007&volume=9&issue=3&spage=300.
- ^ Blackbourne LH. Surgical Recall. Lippincott Williams and Wilkins, 2009. pp169
Drugs for obstructive airway diseases: asthma/COPD (R03) Adrenergics, inhalants Salbutamol#/Levosalbutamol • Fenoterol • Terbutaline • Pirbuterol • Procaterol • Bitolterol • Rimiterol • Carbuterol • Tulobuterol • ReproterolLong acting β2-agonists (LABA)otherGlucocorticoids Anticholinergics/
muscarinic antagonistIpratropium bromide# • Oxitropium bromide • Tiotropium bromideMast cell stabilizers Cromoglicate • NedocromilXanthines Eicosanoid inhibition Thromboxane receptor antagonistsCombination products Adenosinergics Receptor ligands 2-(1-Hexynyl)-N-methyladenosine • 2-Cl-IB-MECA • 2'-MeCCPA • 5'-N-ethylcarboxamidoadenosine • ATL-146e • BAY 60–6583 • CCPA • CGS-21680 • CP-532,903 • GR 79236 • LUF-5835 • LUF-5845 • N6-Cyclopentyladenosine • Regadenoson • SDZ WAG 994 • UK-432,0978-Phenyl-1,3-dipropylxanthine • Acefylline • Aminophylline • Bamifylline • Caffeine • CGS-15943 • 8-Chlorotheophylline • CPX • CVT-6883 • Dimethazan • DPCPX • Fenethylline • Istradefylline • KF-26777 • MRE3008F20 • MRS-1220 • MRS-1334 • MRS-1706 • MRS-1754 • MRS-3777 • Paraxanthine • Pentoxifylline • Preladenant • Propentofylline • PSB-10 • PSB-11 • PSB 36 • PSB-603 • PSB-788 • PSB-1115 • Rolofylline • SCH-442,416 • SCH-58261 • Theobromine • Theophylline • VUF-5574 • ZM-241,385Reuptake inhibitors ENT inhibitorsVNT inhibitorsCategories:- Bronchodilators
- Xanthines
- Phosphodiesterase inhibitors
- InChI=1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2
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